Matthew Parker's Preppie Poster Child Look

College-bound: “If only I had been in college in the 1950s,” says Matthew Parker. “I could have been the prepster poster child.” Alas, the West Seattle–based event planner and designer (his résumé includes everything from gala décor to Skillet Counter’s logo design) missed the style moment by fifty years, but has channeled the same spirit into his collegiate-esque ensembles of cuffed chinos, nerd-tastic eyeglass frames, seersucker jackets and boat shoes. “I really like to take a preppy piece, such as a striped polo, and add in an urban vibe via pattern; like I love crazy socks.”

Best conversation starter: “I hoard these chunky school sweaters from a Catholic uniform store in Tukwila. People always get a kick out of the embroidery stitched with the school name.”